


Winchester's Tribulation

by User24601



Series: A Thousand Unexpected Tribulations [2]
Category: Supernatural
Genre: Anal Sex, Bottom Dean, Dead Dove: Do Not Eat, Explicit Sexual Content, Forced Ejaculation, M/M, Mental Anguish, Non-Consensual Drug Use, Physical Abuse, Rape, Sexual Abuse, Torture Porn
Language: English
Status: Completed
Published: 2018-11-08
Updated: 2018-11-08
Packaged: 2019-08-20 18:46:49
Rating: Explicit
Warnings: Graphic Depictions Of Violence, Rape/Non-Con
Chapters: 1
Words: 3,982
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/16561265
Author URL: https://archiveofourown.org/users/User24601/pseuds/User24601
Summary: Dean Winchester has been taken captive and is subjected to an unexpected tribulation. This event is full of anguish on both a physical and mental level.





	Winchester's Tribulation

**Author's Note:**

> A friend once postulate what would happen if I took my most popular story and changed the fandom... This is the result.

The hunter regained consciousness like an old car sputtering to life on a cold day. Considering the cold hard floor he lay upon, it was an appropriate metaphor. Surrounded by darkness, Dean Winchester hadn’t a clue where he was or how he had gotten there.

Instead, he tried to move. An intense ache thrummed through his core and down his extremities, taking his breath away. After giving himself a moment or two, he made another attempt, this time being careful to slowly adjust his position. As he shifted his leg, he heard the clink of metal upon metal and felt a cold cuff around his ankle. Blindly feeling for the restraint, he realized it was an old-fashioned manacle, heavy and unwieldy.

“Sammy!” The hunter called out for his brother. But there was no answer.

It was then that fear finally crept up and grasped hold of him.

Having had his fair share of run-ins with ghosts, demons, and other supernatural beings, he had become accustomed to dealing with high-risk situations. Fear was just part of his life, and he knew how to deal with it in a manner that kept him level-headed. But in all those other situations, he’d at least had some understanding of the circumstances.

This was different. Not only did he not know where he was or how he had gotten there, but also he didn’t know who was responsible for this. From the pain and subsequent nausea coursing through his body, he surmised he had been drugged. As he yanked at the chain moored to the floor, it was clear it (whatever ‘it’ was) had sapped most of his strength as well.

“ _But for what purpose?_ ” He silently asked himself. “ _Think, Dean, think_.”

If someone had wanted him dead, he would be already. He was alive; so his abductor most likely needed him to stay that way, at least for the time being. Dean tried to slow down his breathing and concentrate. Whatever was in his system was hampering his ability to think clearly. He needed something, some clue, to give him some context of the situation.

The darkness that surrounded him was the first clue, a windowless room. The cold hard floor was the next, a basement.

“ _So no point in yelling or screaming, no one will hear me.”_

The solid cuff around his ankle attached to a short chain bolted to the floor was a strong indication that whoever had him, did not intend on him going anywhere. And yet, his hands were not bound. So apparently, his captor wasn’t concerned that he would possibly be able to undo the restraint. But at least, with his hands free, he could defend himself to some extent, if it came down to that.

Feeling around his person, Dean immediately noticed both his canvas jacket and button-up shirt were missing but he still wore his t-shirt. His jean pockets were empty and his belt and shoes were missing. The shoes and the belt could’ve made potential weapons, so he wasn’t surprised they were taken from him. So no chance of fighting back with those items, he’d have to make do with just his fists.

If Sam were here, he’d say, _“But is that the best course of action? To go on the offensive right away?”_

Slowly pushing himself to a sitting position, Dean shivered as the pain running through him left him light headed and severely fatigued. He sat and contemplated possible scenarios. Acting out in an aggressive manner right away could deprive him of potential means of escape. He was chained to the floor and getting out of this would be a challenge.

“ _Maybe_ ,” pretend Sam contemplated, _“your best chance of getting out of this restraint is to convince your captor that it isn’t necessary to keep you locked up.”_

Eventually, Dean decided his best course of action would be to try and cooperate as much as he could and align himself with his captor. This method would open up more opportunities for escape and he would be able to get the hell out of this basement alive and intact.

Something else was bothering the hunter though. Who had abducted him? He had a long history of pissing off dangerous creatures. Maybe one of them had come back for revenge. Or possibly someone was looking for an easy payday. No, that couldn’t be the reason. Hunters were a penniless group, to begin with, and he and Sam were no exception. Perhaps, they had some artifact, trinket, or book that held significant to his abductor and that is why he was being held captive.

Cradling his head between his knees, he contemplated what was in store for him. Based on past experiences, torture was a likely scenario. Broken bones, missing appendages, sleep deprivation, and other nefarious means of torment swirled in his mind. The longer he spent thinking, the harder it was to remain calm. His stomach churned. Being in such physical discomfort wasn't helping his concentration. Each passing minute did nothing to ease his pain. It left him feeling exhausted both mentally and physically, to say nothing of his ability to perceive the passage of time.

_“How long have I been down here?”_

The sounds of a heavy lock being opened startled Dean from the darkness that filled his mind. He struggled to his feet, leveraging the wall behind him for balance, still feeling the effects of the drug. The grating sound of a heavy door being pulled open was accompanied by the sudden brightness of lights being turned on. The hunter was forced to cover his eyes for a moment as they adjusted to the light. Creaking footsteps coming down the stairs were briefly preceded by the sound of the door above shutting and being locked.

Quickly glancing around at the barren basement, Dean observed more clearly that the floor was poured concrete and the walls were made of cinderblocks. A metal table, a hose, and a drain were the only objects he noticed before his attention was affixed to the persons coming down the stairs. Two young men had descended into the basement and Dean mentally kicked himself for not anticipating that there would be more that one captor.

He recognized them instantly, or at least he recognized the meat-suits the two demons were wearing instantly.

One was exceptionally tall, his hair dark and thinning. His sparse and whiskery beard, touched with gray, and heavily furrowed brow did not detract from the menacing look on his face. If anything, his features only added to his overall ominous appearance. It was Hell’s chief torture, Alastair.

However, Alastair was the least of Dean’s worries when he had seen the shorter man who had followed. His physical appearance was intimidating: broad shoulders and a face no one could forget, a cleft-chin and square jaw. Azazel’s eyes flickered yellow when he made eye contact with the hunter.

As the demons got closer to him, Dean was quick to get to his feet and fall back against the wall, wishing to he was nowhere in the vicinity of the sulfur-reeking bastards. Yellow Eyes had approached first and Dean clenched his hands into fists. He needed to get control of the thoughts raging inside of him before he took action.

“You’re dead,” Dean pronounced. “I shot you with the Colt.”

Azazel did not reply nor did he explain his and Alastair’s sudden appearance. His silence was deafening.

The sound of metal jangling drew the hunter's attention to the other demon, Alastair, who had taken a set of keys from his pocket. Kneeling down, he unlatched the locking mechanism of the manacle around Dean’s ankle.

Azazel stood unwaveringly eyeing their captive, waiting for Dean to take that swing. Knowing full well that it would be the older Winchester’s first reaction. However, Dean was not an idiot. He knew that the door above was most likely locked and he would have to get the keys in addition to physically fighting off both of the demons. In his weakened condition, he didn’t stand a chance.

 _“Where is Sam when I need him?”_ he wondered.

As Alastair stood back up, Dean spat, “And you. Sam ripped you apart. How are either of you here?”

He was answered by Azazel quickly grabbing him by his hair and smashing his head against the wall behind him. Crumpling to the floor, the jarring pain in his head left him dizzy. He put his hands up defensively. The pair moved in a coordinated fashion as they picked him up, on either side, drug him over to the metal table, and bent him over it face down. All the time, never saying a word.

Trying to push up off the table but finding himself even further weakened by the blow, Dean came face to face with Azazel. As Yellow Eyes came around the other side of the table and grabbed his wrists and held them down against the cold metal surface. Dean turned his head and looked over his shoulder as he heard the swish of a blade being sprung from its handle. Seeing Alastair and the large pocket knife he held, he began to wonder which extremity he was about to lose.

The blade was pressed against his skin and Dean squeezed his eyes shut as he attempted to preemptively steady himself against imminent injury. However, instead of cutting flesh, Alastair began to cut his clothes. His shirt was gone in a matter of seconds, shortly followed by his jeans and boxers. Dean’s legs began to buckle as Alastair slid his hands down sensuously and grasped each ankle and pulled off his socks.

“You can’t be serious,” Dean gasped as he realized that it might not be mere physical torment these demons wanted from him but his body. A possibility that had not entered the hunter’s mind previously because very rarely, if ever, did straight men get raped, especially not by demons who were supposedly dead.

 _“Raped!_ ” The thought echoed in his mind, _“I’m going to get raped!”_

Dean became astutely aware of Alastair’s lingering touch behind him and the hungry look in Azazel’s eyes in front of him. Any thought of cooperation he’d held before completely disappeared. Despite the physical limitations imposed by whatever drug he’d been given, he began to struggle in earnest.

However, Azazel had superhuman strength and his grip upon the hunter’s wrists remained firm.

Trying to kick at the demon behind him he found every movement sapped him of more strength. Dean’s heart hammered as he heard the sound of a zipper being undone. Alastair had unzipped his pants and had pulled out his considerably large member. He then licked his hand to lubricate it before rubbing himself to erection.

"No," Dean stuttered, "no, you can't. I'm not... I've never... You can't. No! Don’t!”

His pleas fell on deaf ears as Azazel held his wrists firm and Alastair kicked his legs apart. Trying to get a footing and move away from the demon approaching from behind, his damp toes, wet from the sweat of his fear, slipped on the smooth concrete.

But Alastair was unyielding as he grabbed his hips and pried apart his ass cheeks with his thumbs. Feeling the head of Alastair’s cock against his sensitive hole, Dean cried out, “PLEASE DON’T!”

This desperate cry for mercy did not sway the demon from his actions. Instead, Alastair pushed the head of his cock through the clenched ring of muscle. Dean screamed!

What physical discomfort he had felt before vanished in the wake of this new stabbing pain that surged in his rectum. Dean had known the word ‘violated’ before but now he truly understood its full meaning. Trying to squirm away was to no avail as the demons had too strong of a hold. Alastair’s cock made its way deeper and deeper into him before pulling back out again.

His rapist had started slow but had picked up the pace and he rammed his cock in over and over, again and again. With each push, the breath was driven from Dean’s lungs and he gasped for air as Alastair partially pulled out. The demons continued to ignore his cries of ‘no’ and ‘stop.’

Pain and humiliation were all Dean felt at first but then he felt warmth running down his bare legs and smelled blood. Fresh shame washed over him knowing he had torn like a virgin bride on her wedding night. Worse, the slickness from his bleeding just made it easier for Alastair to pick up the pace.

 _“This can’t be happening,_ ” the thought flashed Dean’s mind. “ _It can’t be real.”_

But real it was.

Looking first at the hands still holding his wrists down on the table, Dean slid his gaze upward and locked onto Azazel’s dark eyes. He wanted to beg the demon in front of him to make Alastair stop. However, the way Azazel was looking at him made his blood run cold. Clearly and sickeningly, Yellow Eyes found the sight before him very arousing.

From the periphery of his vision, Dean saw a hand reach over for Azazel. Glancing up, he distinguished a soft smile on Alastair’s lips as he looked at his accomplice lovingly. ‘Soft' and ‘lovingly’ were two terms vehemently at odds with the vicious manner in which Alastair was pounding into him.

Gagging at the mere idea of the demons being in some sort of twisted relationship, Dean watched Alastair tenderly brush Azazel’s short bangs back, gently running his hand through the short-brown locks, and then coming to rest at the back of Azazel’s head.

Affectionately, Alastair pulled Azazel towards himself and the two demons came together, right above the hunter’s bowed form, lips brushing together in a most tender fashion. For a few moments, Alastair’s rhythm faltered, making each thrust even more agonizing while the rapist was otherwise engaged.

Dean could hear the sounds of their mismatched, heavy breathing coupled with the wet sounds of tongues and the occasional click of teeth coming together. He wanted to fight more but his body wouldn’t obey him. He felt so heavy, immobile. Putting his face down on the table in sheer and utter defeat, he closed his eyes. Tears trickled down his face and onto the metal surface beneath him.

He was done. What point was there in resisting anymore?

Wanting to retreat, to go somewhere else, even if it was just in his head, he closed his eyes in an attempt to shut out the situation. However, this action did nothing but to heighten the physical sensations and kept him in the present. The hunter could not avoid the pain of Alastair hammering his ass, the feeling the table’s edge digging into his hips, the rough texture of the man’s jeans against his bare bottom, or the calloused hands firmly gripping his smooth skin. Perspiration fell on him from above but oddly, the worst sensation was that of Alastair’s balls slapping into the sensitive skin of his perineum over and over again.

For what felt like an eternity, Alastair fucked Dean, using the hunter’s tight virgin asshole for his own pleasure. Enjoying the pain and suffering he inflicted he raped Dean like a fucking whore. Finally, Alastair slowed his pace as he bucked his hips, unleashing and painting their captive’s insides with cum.

A feeling of relief rushed though Dean when he realized Alastair finished. Just as this thought entered his mind, the two demons released their grip on him and he slumped to the ground.

It was only then that Dean realized his cock was hard. Apparently, the sensation of rubbing up on the table and the pressure on his prostate had given him an erection. Shame replaced the previous moment’s relief and he tried to cover himself up with his hands. Walking around the table, Azazel stood over him. As Dean looked up he saw that same arousal from before and realized the pair was not done with him yet. On his hands and knees, the defiled hunter tried crawling away, only to find Azazel already had a hold on him.

Picking up what remained of Dean’s shirt, Alastair wiped the blood and cum off his dick before tucking himself back into his pants. He then helped Azazel put their weakened prey back on the table, this time on his back. Dean tried to roll onto his side, grasping at the edge of the table with his fingers but Azazel was already between his legs and holding them pushed back towards his chest and apart. Taking the same torn piece of fabric he had used to wipe his dick, Alastair shoved this into Dean’s mouth.

At the taste of blood, cum, and traces of shit on the cloth, Dean retched and bile rose up in his throat. He had to get the makeshift gag out of his mouth but try as he might to push off his attackers, he simply did not have the physical strength and his efforts were to no avail.

Climbing onto the table behind Dean’s head, Alastair pulled up his arms up and knelt on them to secure them in place. Then he reached forward and grabbed Dean’s legs, effectively pinning him to the table, leaving Azazel free to take out his dick.

This time Dean couldn’t scream as he was raped. Whether or not the second demon’s cock was bigger than the first, he didn’t know because his anal muscles were shot from him trying to clamp down and prevent the first attack. Azazel certainly felt bigger, because this time around the pain was even more excruciating.

But instead of just using the hunter like his partner before him, after establishing a rhythm, Azazel reached forward and wrapped his sweaty palm around Dean’s dick. The sensations were too much and Dean’s body involuntarily responded to the touch.

A muffled moan escaped the gag as Dean tried to resist the surges of self-loathing pleasure as Azazel jacked him off while assaulting his abused hole. To make things worse, sliding his dick in and out of him, Azazel was deliberately hitting that one spot inside at just the right angle and with just the right amount of pressure. This combined with the hand around his cock left Dean shuddering with both pleasure and revulsion.

 _“No!_ ” Dean was in disbelief that his own body could betray him in such a way. “ _Not this. Please God, not this_.”

The demon raping him neither noticed or cared for his perspective on the matter as Azazel continued his assault. Soon Dean’s balls began to tighten as he felt the pressure within them start to build.

“ _Hold on,_ ” he told himself, trying to steady his resolve. “ _Don’t let him do this to you. Don’t give them the satisfaction. Don’t cum. Don’t let them take this from you too.”_

But they did. Soon the sensations overpowered him. His cock spewed ropes of semen onto his belly and chest. Any feelings of pleasure immediately evaporated as he came crashing down from his climax back into the moment. Azazel was still inside of him, still fucking and tearing up his ass.As the thrusts became irregular Dean hoped his rapist would reach orgasm soon. Holding onto the back of his thighs, Azazel shivered as he filled Dean with cum.

Once Azazel was done, he let go and removed his still semi-hard cock from the hunter’s bleeding anus. Alastair immediately pulled Dean off of the table and let him fall to the floor. Barely getting an arm out in time to keep his face hitting the floor, their victim just laid there, barely seeming to even have the strength to spit out the soiled rag that had been stuffed in his mouth.

Totally shocked at the events that had just transpired, Dean grappled with his emotions. He didn’t know what to do. All the fight had been fucked out of him. He was left violated, humiliated, ashamed, dirty, and broken. _“They raped me,”_ repeated in his mind. _“They took turns raping me and I… I’ve just been raped! Twice!”_

Feeling completely drained Dean lamented the fact that he hadn’t been able to stop the attack. What’s more, he was completely mortified that not only had he gotten an erection but he had ejaculated at the hand of his rapist. This knowledge was pure anguish and was easily one of the worst things he had ever felt in his entire life. Mind flashing for a moment on his deceased mother, Dean had a sudden urge to call out for her despite the fact she’d been gone for years now.

His humiliation was made utterly complete when the demons walked back over and dragged him over to the basement’s floor drain and started to hose him off. But no amount of water could wash away the shame that had taken a hold. The cold water hit him hard in the face, taking his breath away. Then the stream of water moved down his body striking the bruised and broken skin.

As the water worked its way towards his more delicate regions, Dean bit his lip to prevent himself from crying out at the sharp pain that emanated from his damaged ass. The coppery taste of blood filled his mouth as he watched the rivulets of red-tinged water from his other bleeding slowly make their way over the bare concrete and disappear down the drain. Though he knew his body would slowly heal the torn tissues inside, something else had been rent during his assault, something that might never mend.

Limp as a rag doll, the hunter hung in the demons’ grasp as they hauled him back over to the spot on the ground where the shackles lay bolted to the floor and once again fastened the cuff to his ankle.

Behind closed lids, anxiously, Dean listened to the sound of their steps retreating as they ascended the stairs and slammed the door shut and locked. A second later the lights were turned off and he was plunged into total darkness once again. Blinking his teary eyes back open, he was glad he couldn’t see in the dark. He had no desire to look at the table across the room, a monument to his rape.

Shivering uncontrollably, he curled up naked in the dark. Then the tears came again. Slowly his tears turned into sobs of grief that racked his whole body. His mind whirled with unanswerable questions and implications.

_“How could this have happened? Those bastards, they took my freedom and my body without even saying a word. I was their plaything”_

He tried to brush these words away, attempting to deny what had just happened. No sooner had he pushed this aside than an even more horrific realization invaded his mind: that as long as the demons had him, what he’d just endured could easily happen again.

_“If they can keep me weak like this, they’ll be able to do whatever they please until someone else can stop them.”_

This last thought left him shuddering in revulsion.

_“Surely Sam knows I’m missing. Will he be able to find me here? How long will it take him? What will he say if he finds out that I let the demons rape me? Sure I struggled and resisted the best I could but I failed. What good is a hunter who can’t keep himself safe? I don’t feel like a man. I just feel pathetic.Fuck… I am pathetic.”_

A new wave of tears washed over Dean as he lay in his dark despair. As he cried himself out, however, his tears washed his anguish away revealing the rage beneath it. His anger had always been his anchor and Dean latched on to this immediately. So he’d been beaten this time, that was clear, he told himself, and maybe he was pathetic. But he was not completely broken.

At least not yet.

 

**Author's Note:**

> Thank you so much for reading! If you liked what you read or you have any feedback, please leave me a comment. Perhaps, you might have a suggestion for the next fandom I apply this treatment to...
> 
> Additionally, if you would be interested in seeing this scenario play out, then you can swing over to the work that inspired this one, [Unexpected Tribulations](https://archiveofourown.org/works/11712039), and see how everything unfolds. It’s not Supernatural but prior knowledge of the fandom isn’t necessary. I promise, you won’t be disappointed.


End file.
